A bit player named Jon Hamm!
And even if she can, is that enough?
Some decried the film’s conclusion, in which 20-year spoiler alert!

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the two heroines break up.
But it still marked a milestone for lesbian and queer representation.
Everybody was asked to do something they didn’t know how to do.

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We both ended up writing a sketch that was about a horrible date, and we clocked each other.
We stayed in touch after that retreat.
Jen and I regrouped and said, “What if all the bad dates is act one?

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These two women are going crazy in the dating scene, it’s not working.
And then act two is after they get together?”
So, we were suddenly thrust into screenwriter-ville and the development world.

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We got bounced around so much that we said, “Let’s just make it indie.
Let’s get a camera.
Let’s get some cash and just do any version of this we can.”

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People watching true indies don’t realize how much goes into the hustle to raise that money.
It was really a grueling period.
We made something beautiful and enduring.

Courtesy of Eden Wurmfeld
Director Charles Herman-Wurmfeld was still very green, but he was passionate about the script.
I was ready to come and do craft services if necessary.
WURMFELD:As his sister, I can say he was not at the top of the list.

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LAWRENCE SHER (Cinematographer):Kissing Jessica Steinhas such an important place in my history.
A friend of mine connected me to Jen, and then got me a chance to meet with Charlie.
Jen met me at an airport restaurant.

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That I was just going to give a shot to make myself be a cinematographer.
Here it was September, and I hadn’t earned a single dollar that year.
I was freaking out a bit.

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WESTFELDT:Jon had [played Josh] in the play, but he wasn’t available.
He was on this show calledProvidenceat the time.
So, we started the audition process.

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JUERGENSEN:Scott at that time was “offer only “for a project like this.
And we were like, “Oh gosh, it’s such an important role.
hey, hey, hey read for us.

Courtesy of Eden Wurmfeld
We just want to hear it.”
And Scott, you very graciously read for us.
SCOTT COHEN (Josh Meyers):Yeah, I remember that.
I don’t really get it.”
But that was that.
I had no idea who he was.
On May 11th, 1996, my father Sidney died.
And he was the king of my life.
I was alone with his body in White Plains hospital.
There was a knock on the door.
And it was my assistant who had worked for me for only 90 days.
And Jennifer said, “I didn’t want you to be alone with your dad.”
Later, Jennifer asked me to come see her play.
I said, “I give my word.
I will play your mother, but you better give me more material.”
With the cast and crew assembled, they set about filming on location in Connecticut and New York.
WESTFELDT:We always said that the city was another character in the film.
And to shoot in real locations and all of those things.
WESTFELDT:We didn’t shut down a street.
We were in the street, and it was a green light and we’d go, “Go.
Roll the film.”
I’m trying to hail a cab, and we’re almost getting hit by cars.
HERMAN-WURMFELD:We should tell the story about the taxicab.
JUERGENSEN:This is where Helen and Jessica are discussing the lipstick.
HERMAN-WURMFELD:We just hailed a cab and jumped in.
SHER: Charlie was stuffed next to the driver.
The camera was in the middle, right between the seats.
Basically, the sound person was in the trunk.
Just go with it.”
These guys from the street watching just kept yelling out, “Hey, pregnant lady.
Hey, pregnant lady.”
And Charlie said to me, “Okay, don’t do that.”
SHER:There was a screening right before 9/11 and then there was another one after in Toronto.
And the one after was just fundamentally too hard to watch.
JUERGENSEN:People were audibly loudly gasping in the theater.
HERMAN-WURMFELD:It wasn’t like they were just there.
We were utilizing the towers to represent these two iconic characters.
And so, there were gasps in the audience every time we went there.
It was a lot.
WESTFELDT:There were eight shots of the towers.
It was an incredibly difficult decision [to remove them].
All of us were on email threads about it.
There were pros and cons to leaving them in.
I know we were all tortured about it.
Some guy who was just like, “Haha, I’m in a movie now.”
And we’re like, “We’re actually shooting.
Could you c’mon not do that?
We don’t have a minute to spare.”
Because our days were so tight.
WESTFELDT:In that same sequence, I was totally new to camera.
I was only a musical theater and theater person.
We were getting changed and in hair and makeup, so we had wet hair.
Charlie ran in and was like, “The light’s beautiful.
Larry wants to shoot a wide shot of you guys arguing as you cross the street.”
And we were like, “What?
We’re like, “We have curlers in, and we were not dressed.”
And Charlie was like, “This is important to Larry.”
We were like, “We’re going to look ridiculous, but all right.”
You couldn’t tell that our hair was wet.
It just looked like a beautiful shot.
SHER: I probably was a little bit less tactful.
I was like, “Get them out.”
We had limited lighting.
Heather, do you remember how we came up with that ending?
Why is she even on the date?
It was outlandish for that character.
It was tricky though.
I think it was 13 pages.
That’s too long for one scene, but it was this ebb and flow of little scene-lets connected.
We felt that this is really the crux of the movie right here and we better get it right.
WESTFELDT:Heather remains the only girl I’ve ever kissed.
JUERGENSEN:At that point, Jennifer and I were like an old, married couple.
We had been developing this script for so long.
We had done so many workshops.
We had done that particular scene of the montage of like, “Should I touch you?
And is it tongue?”
And all that throw in of stuff.
That was really all the way back to the play; it was one scene in the play.
In a weird way, we had to act like it was more uncomfortable than it was.
And it would always get a laugh.
It’s just funny how it evolved from the sketchier version to the subtler version.
As things develop, Jessica struggles to keep her relationship with Helen a secret.
HOFFMAN:I haven’t had a part like that before that or since.
I remember running around in this Upper West Side apartment shrieking, and it was just so cool.
It felt like the joy you feel of being on the stage.
HERMAN-WURMFELD:Oh, I remember that day, Jackie.
It was a beautiful day.
I remember our conversations behind the scenes.
And that agreement we made to let it be free.
HOFFMAN:To this day, lesbians stop me on the street and say, “Lesbians?”
It’s become this iconic moment.
WESTFELDT:That was another borrowed apartment.
My dear friend, Haley, her old studio apartment.
Almost every location was somebody’s that we knew.
WURMFELD:It was absolutely that building.
It was the Upper West Side.
They were like, “you’re able to’t shoot here anymore.”
So, we had some very pissed off neighbors.
FELDSHUH:I think it was two in the morning.
HERMAN-WURMFELD:It was.
It was the last of the day.
FELDSHUH:And we were at Jennifer’s mom’s house?
WESTFELDT:My mom’s friend.
FELDSHUH:I remember resting and being awakened to do the scene.
Sometimes it’s hard to watch yourself in films.
This was an incident in my career where I thought I was better than I remembered.
I loved the constriction of it.
I loved Charlie’s gentleness with it.
I love the demands that we had to shoot it quickly.
That scene was a gift.
That scene has gotten me acknowledgement and has been a hallmark in my work.
This is such a beautiful moment.”
I remember thinking, “If the whole movie’s like this, then we got something.”
HERMAN-WURMFELD: I remember that too.
Just sitting there going, “Something awesome just happened.”
Tovah, you became like the moon herself, just beaming love.
Jessica and Helen resolve their fight, and Helen comes with Jessica to a family wedding.
WESTFELDT:We were in the armory in Central Park and they had never had a shoot there before.
Jon’s friend worked for the Parks Department and pulled some strings.
All of our friends and family were the wedding guests.
It was not unlike the shot with the wet hair, where we were just waiting for magic hour.
Scott and I had a lot of chemistry that we built through the shoot.
It was so easy to play off each other.
That’s just so much the way life is; that the timing is just slightly off.
And then life changes.
I remember the night sky and the city behind us.
WESTFELDT:There was so much chemistry between Heather and Scott as well.
It felt like a very powerful triangle.
Later, potato."
COHEN:I think we need to do aKissing Jessica Stein 2,just saying.
The two don’t end up together, but they remain friends.
But the main thing we wanted to land was their friendship.
Whether or not Jessica was going to get together with Josh, who knows?
We just wanted to show the changes and end on the two women as thick as thieves.
It doesn’t feel right the way Jessica ends."
And that was the real catalyst for, as a team, discussing all those things.
HERMAN-WURMFELD:It was subtle changes.
JUERGENSEN:Jessica was more nervous when she ran into Scott’s character.
A little more like still the old Jess.
Jennifer referred to it as “the curly-haired scene.”
HERMAN-WURMFELD:This is why we love this character, because it’s a liberation story.
And that is such a beautiful offering to the world.
WESTFELDT:My classmate from college [plays the other girl] in that bookstore scene.
JUERGENSEN:The revised version of the bookstore scene honored more what had transpired between Jessica and Helen.
At the time, we had a lot of blowback about it.
But it was important for us to show two different stories here.
One where Helen is like, “This is who I am.
This is my identity.
It’s not a choice for me.
It’s not fluidity.
It’s who I am.”
And the scene where Jessica’s saying like, “But we’re best friends.
This is the best relationship I’ve ever had.”
Essentially like, “Isn’t that enough?
I love you so much.”
And it wasn’t enough for Helen because she really needed that sexual chemistry and that passion.
The difference in their experience of it was an important distinction to show.
JUERGENSEN:To me, the reality that these two women had very different experiences of this relationship.
So, she couldn’t be with this person for the long haul.
My character, on the other hand, was gay.
She had been with men because that’s societally what is the starting point.
But when she explored it, for her it was a revelation.
For my character it was, “Oh, this is who I am.”
WESTFELDT:I felt like Jessica would’ve stayed in it forever though.
Because she loved her and that was enough for her.
HERMAN-WURNFELD:Many queer people come out with their more straight best friends in sexual relationships.
Now, after 20 years have passed, you’re seeing that fluidity in action.
Kissing Jessica Steinis streaming now on Hulu.
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